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Disparaging the dead is supposed to be taboo, but what if those dead were real jerks in life? In his new book, “Speaking Ill of the Dead: Jerks in Boston History
” (Globe Pequot Press), Paul Della Valle’s definition of “jerk” is pretty loose. Among his portrayals are Harry Frazee, the man who sold Babe Ruth from the Red Sox to the Yankees, notorious schemer Charles Ponzi, James Michael Curley, Albert DeSalvo, and Charles Stuart. Della Valle examines why these historical figures became jerks in his mind, whether it was because of abuse or just plain old greed. The Globe spoke with Della Valle about why he decided to write this kind of book.

Q. You were first a journalist, then an author, and now a high school teacher. What made you want to change careers?

A. I was a journalist for 30 years and owned a small newspaper. After 10 years of running it, I sold it to the Boston Herald. I started writing a book, and at the same time one of the people I was writing about was Horace Mann; everything he said struck home with me. I took the MTEL [Massachusetts Tests for Educator Licensure] test and became a teacher. Everything that Mann, the secretary of education and father of public education, said in the 1830s about education takes place today. I love teaching, but I do miss being a journalist.

Tom HERDE/GLOBE STAFF/FILE/1989

Police examine the car where Carol Stuart was shot.

Q. What made you want to write nonfiction instead of fiction?

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A. As a journalist, I am used to research and writing the truth. Joe Palmer was persecuted for wearing a beard. I wrote about him while being a columnist for the Worcester Telegram. I used that as a sample chapter [for his 2009 book, “Massachusetts Troublemakers: Rebels, Reformers, and Radicals from the Bay State”] and was told to go with it.

Q. Your publisher, Globe Pequot Press, asked you to write “Speaking Ill of the Dead: Jerks in Boston History.” Do you think it was the journalist in you that made you want to show both sides of these jerks?

WIDNER LIBRARY AT HARVARD UNIVERSITY via AP

An illustration of John Webster assaulting George Parkman in 1849.

A. It goes back to being a journalist. I always try to show both sides. It’s hard to feel bad about the Boston Strangler but he had a tough childhood. His father was abusive. He watched his father bend his mother’s fingers back one by one until they broke. That’s why he turned out that way. Charles Stuart had a normal upbringing but something made him incredibly evil. It was a case that people around Boston recalled vividly. He fooled all of us and it was just terrible.

A. One of the guidelines set by the publisher was that the person had to be dead for 50 years. [However, not all of those written about in the book have been dead for that long.] Basically, I just cast a broad net and got different types of jerks and serial killers.

Q. You explain in your book that Dr. John W. Webster owed money to Dr. George Parkman. Parkman hounded Webster for the money. Do you sympathize with Webster because of that?

A. Yes, Parkman sounds like the biggest rich jerk in the world. It was said that he would take a widow’s last dollar that she owed him for rent.

Q. You have serial killers, sociopaths, and schemers featured in this book. Why do you include Harry Frazee, who was none of the above?

GLOBE FILE PHOTO

Harry Frazee, the Red Sox owner who sent Babe Ruth to New York in 1920..

A. Because of the whole Boston thing, selling Babe Ruth. We love our Red Sox, he committed a mortal sin. If it was true that he was trying to be driven out, as he claims, then I feel bad. We thought we would never see another World Series. The “Curse of the Bambino” was overwhelming for Red Sox fans. He had to be in the book because of that one event. It would be like if they just traded Tom Brady tomorrow.

Q. How was the research process?

A. I enjoyed doing the research, especially when I had time during a school vacation. Research is a lot of work but if you enjoy it it’s not bad. And sometimes you read things that are totally the opposite of what you previously read. History is volatile; it is different depending on whom you ask.

Q. How long did it take to research and write this book?

A. I did it in a year and a half. For long periods of time I wouldn’t do anything. But on school vacations I would do it every day for six to seven hours.

Q. What was the most challenging experience while researching and writing this book?

A. Finding a good photo of [serial killer] Jane Toppan. Most of the time I could get them from the Library of Congress. But not much was written about her.

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